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For its much-anticipated first outpost outside London, the hip Hoxton boutique hotel brand—named for the trendy hipster neighborhood of its first hotel—chose five 17th- and 18th-century townhouses (including a former mayoral residence) on the canals of the Dutch capital. The brand has a formula that works, but rather than impose its signature style on another city—colonial-style, if you will—the designers have done it the other way around, imposing the buildings’ architectural styles and the city’s aesthetic on the brand. Original parquet floors, beamed ceilings, and wood paneling infuse the midcentury leather furnishings, geometric mirrors, and creatively patterned subway-tiled bathrooms with a Dutch feel, while the turquoise of the canal outside is reflected in the paint. Two rooms have original ceiling frescoes, and five have (non-working) fireplaces. In the ways that count, The Hoxton is true to its brand, such as bespoke toiletries, a scenester restaurant, a trendy bar, and its signature daily breakfast bag with a banana, granola, and orange juice.

A 1920s townhouse in Brussels’ well-heeled Châtelain neighborhood, the intimate, Fellini-inspired Odette en Ville might as well be your fashionable Belgian friends’ pied-à-terre in the European capital. Its older sibling, Chez Odette, a landmark restaurant and inn, is hidden away in the tiny village of Williers, on the French-Belgian border, and when the Brussels iteration opened, it dressed up with all the panache of a newer arrival: a little bit flashier, a little bit sleeker, a little bit more urbane. Its marble bathrooms, dark walls, and chrome accents all feel very grown-up, but roll-top tubs, fireplaces, and vintage decor reveal those homey country roots, as does the fresh, unpretentious cuisine, including the homemade jam at breakfast. With just eight rooms, the hotel feels intimate and private, an atmosphere only enhanced by the private library, a cozy lounge (notably, adjacent to the bar) with overstuffed leather Chesterfields, vintage chess sets, shelves of art books, and a working fireplace.

If big museums aren’t your thing, but you’d like to get a flavor of the story of Dublin, drop into the Little Museum on St. Stephen’s Green, which is full of quirky memorabilia from times past in the city, all donated by the public. There are guided tours on the hour, and each tour reveals some of the city’s secrets, with letters from famous literary characters like James Joyce and Samuel Beckett, signed U2 albums, and all sorts of things on display—from badges and newspapers to old signs and even bullets—all of which have a story to tell. Set in a Georgian townhouse, with views out over the green and the excellent Hatch & Sons Irish Kitchen in the basement for post-tour grub, this little space offers a lot to love.

A trip up to the Dee Wright is a required trek for all my guests who visit Oregon. If you want to experience the power and beauty of the planet, the Old McKenzie Highway delivers an eyeful. Starting in Ponderosa Pine forests and climbing to 5,300 feet above sea level, the road wages a mighty battle to deliver travelers to the top. The structure at the pass is built out of lava from the surrounding flow and towers above the old wagon road that is now Route 242. The road is closed in winter, but it’s a busy corridor during the summer tourist season. The observatory has windows which become frames for the famous peaks easily seen across the barren landscape. On the top deck you can easily see Mt. Hood to the north on a clear day. An interpretive trail gives visitors a great geology lesson on Cascade volcanology. It is a very harsh environment with the blistering heat of summer and the raging snow storms of winter. One can hardly imagine moving though this moonscape in a covered, ox-drawn wagon back when Oregon was just a territory. Nothing like it.

As we arrived in Arraiolos, in the Alentejo area of Portugal, we saw the 14th century castle and the 16th century church resting majestically up on the hill overlooking the town. Arraiolos is known worldwide for its gorgeous woolen carpets which are made in Moorish cross stitch designs. This industry has flourished in the town since the 17th century. We wandered through town as happy tourists investigating this historic site. We watched as the women wove their beautiful carpet designs and chatted with each other. We sat in the town square and sipped a cool drink and observed residents come and go. The restaurants were on every corner so dinner was no problem. This tiny town was a delight with its carpet factories, many shops, restaurants, churches and museums. We investigated each attraction. The buildings were painted white stucco with bright blue trim and Arraiolos resembled a picture book village. Our stay at the Pousada da Nossa Senhora Assuncao was a memorable experience. This stunning 16th century pousada was formerly a convent. It afforded all of the modern conveniences while retaining the serenity and beauty of 16th century Portuguese architecture. Our trip to Arraiolos was another fulfilling travel experience. There was so much to see and to learn about Portuguese history and architecture in this little gem of a town.

Some 35 minutes by boat from Providenciales, sitting all alone on a 1,000-acre island with three miles of white-sand beach, Parrot Cay attracts a seriously moneyed clientele who care, more than anything, about its exclusivity and its spa. Parrot Cay is not exactly monastic: the long list of celebrity visitors has included Jennifer Garner and Ben Affleck (they got married here), as well as Paul McCartney, Julia Roberts, Jerry Seinfeld, and Liam Neeson. But the spa, COMO Shambhala Retreat, is so successful at projecting a holistic way of life that a sense of peace and harmony embraces the entire resort. The central garden-view and ocean-view rooms, three minutes’ walk from the beach, are acceptably chic, but the beachfront suites and villas are knockouts, and the handful of private homes for rent, some owned by celebrities (Christie Brinkley, Donna Karan), are in the fantasy category. The food, by a chef whose résumé includes a Michelin star, and the service, performed by private butlers for some room categories, are of commensurately high standards.

Though my favorite Provencal hotel is now gone from Saignon, it is still the quintessential, hilltop town worth visiting when you’re biking, hiking or driving through this area of France. The dreamy town center (all of three streets) will provide you with views of this fountain, as well as the gorgeous Luberon Valley. The small church in town is a pilgrimage stop for those walking from Rome going to Santiago de Compostela in Spain. No place in Provence ever stole my heart quite like Saignon did. It’s a quiet place with just one bakery in town and only a handful of restaurants, but it has plenty of charm. For a great walk and the best view around, follow the sings for ‘the rock’. Due to its height and location in the valley on this rock formation, Saignon was used as an ancient observatory and a signal station.

In the heart of old town Kapaa, the Olympic overlooks Main Street with laid-back Hawaiian style. Upstairs in an old building that’s been converted into a collection of ragtag shops, the cafe has a commanding presence. Park and wander along the street to make your way to the stairs leading up to the bar and cafe. No pretense upon arrival. The tables lining the open windows in front are choice for people watching and catching the breeze from the prevailing trades. Late afternoon sun streams in and heats things up but is a welcomed delight. There’s always something cold close by to help with the temperature regulation. The bar is a mix of locals and tourists. Happy hour is a draw from four to six with discounts on drinks and select appetizers. I’m a big fish fan when near the source and the fish tacos at the Olympic take the gold. Dressed with a mango salsa and sides of beans and rice, they use two kinds of fish to keep your tastebuds guessing. There is a good selection of island beers and all the fruity umbrella drinks you can imagine. It’s right on the Kapaa multi-use path, so you can cruise in on your beach bomber for a refreshing break. Staff are friendly and service is casually good. Worth a stop when trolling around Kauai for someplace to take a break from vacation.

For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas would not look out of place on South Beach. Nor would the crowd that hangs around its infinity pool or in its restaurant, Mike’s Supper Club, where local musicians and the occasional celeb sit down to knock out tunes on the 1917 Ferrari-red grand piano. The Trident Castle, a kind of fantasy annex, is a former private residence whose grand rooms, sea-view terraces, and dollhouse-size chapel make it ideal for destination weddings. A hard road to get there? Not for guests who avail themselves of the helicopter pad.

Does this setting look familiar? Picturesque Whitehaven Beach on Whitsunday Island has stood in more than once for the perfect island paradise. The sand here is dazzlingly white, thanks to a high percentage of silica crystals. Explore the region on one of many possibly day excursions arranged through qualia. Walk along the more than four miles of stunning beach, snorkel in the pristine waters directly off the beach or enjoy a scenic helicopter flight soaring high above the islands.

In 2009, Caleb Pedersen made a backpack. He wore it around town while riding his bicycle to and from work, hanging out with friends, etc. Little did he know, his bag’s exposure would lead to other people asking, “Where’d you get that bag?” So, he started making bags, which led to the launch of his brand: Chapel. All bags are handmade in the Chapel workshop at the Woodstock Exchange. In fact, you might just bump into Caleb when you visit the shop. Everything they use to craft their bags is sourced from South Africa. Bag designs are functional and universally stylish, so you’ll look good in Cape Town and everywhere else your travels may take you.

A two minute walk from the bustle of downtown Calgary, Prince’s Island Park—which is surrounded by the Bow River—is home to festivals all summer long. The Calgary Folk Music Festival and 52,000 of its closest friends rock and/or folk out on the park the last weekend of July.

If you’re looking for tropical tranquillity, bypass Maui’s buzzy resort enclaves and head away from the coast to the island’s laid-back Upcountry, where you’ll find Lumeria. At the 24-room wellness retreat, visitors can start the day with a guided sunrise meditation, then strengthen their yoga practice, learn to hula or surf, and go snorkeling off the North Shore. Spa treatments include Hawaiian massage and acupuncture as well as nontraditional therapies like crystal healing and shaman-led journeys. The schedule is flexible, so you’ll have plenty of time to learn about Hawaii’s paniolo (cowboy) culture or just take in the ocean views from your private lanai. Guest rooms feature art by local Maui artists, four-poster beds topped with organic linens, and stone-tile showers stocked with Aveda products, while the Wooden Crate restaurant prepares farm-to-table meals with nearly 200 types of fruits and vegetables that grow on the property.

Ningbo’s Old Bund was the place where historic British and Dutch traders lived and you can still see remaining architecture. The swooped lines of Chinese-style buildings are replaced by old stone buildings with familiar details. Also known as Laowaitan, the area is now a lively street full of bars and restaurants. In the evenings, find bamboo sticks of vegetables, seafood, and meat grilled over big chunks of charcoal and smothered in spices—the perfect snack after a few drinks at the Old Bund.

Turtle Inn is one of two upscale resort properties in Belize owned by American movie director Francis Ford Coppola. (The other is Blancaneaux.) This inn is in the town of Placencia, but despite its proximity to the town’s services, the privacy afforded by the resort makes guests feel insulated and more isolated than they actually are. The cabana-style accommodations are luxurious and spacious, with high ceilings and exceptional attention to design detail. The architecture blends in with the environment, but inside the cabanas and villas, guests will feel as if they’ve been transported to another part of the world. The decor is inspired by Bali, with hand-carved wooden wardrobes and trunks and richly embroidered textiles and tapestries. These sit alongside ultramodern amenities and conveniences, such as Delonghi espresso machines and iPod docking stations. Common areas include a triangle-shaped, infinity-edge pool and a gift shop with pricey luxury goods, including handbags and clothing.